Using Kehinde Wiley's Rumors of War as a starting point, this thesis seeks to craft and engage in a larger dialogue about the complex global entanglements of art, trade, slavery, war, commemoration, and race that have existed since the first contacts between Europe and Africa. In September 2019 in New York's Time Square, Wiley unveiled the monument to be permanently installed outside of the Virginia Museum of Fine Arts in Richmond, Virginia. This large work shows a black man in contemporary dress on a horse, created to counterbalance the ubiquitous Confederate equestrian monuments of the south. While this is an important step in the ongoing debate about public monuments of the United States, the equestrian depiction of rulers and warriors has not always been limited to white men. In the sixteenth century, the Edo peoples of Nigeria depicted their ruler, Oba Esigie, atop a horse in the bronze plaque Equestrian Oba and Attendants, now at the Metropolitan Museum of Art. Through material and iconographical analysis, I will show how the Benin plaque signifies peaceful relations and trade with the Portuguese. This interaction also marks the beginning of the transatlantic slave trade, which informed the dehumanizing beliefs of the commissioners of Confederate monuments as well as the colonizers who ultimately removed the plaque from Africa altogether. In this way, the histories embedded within the plaque can serve to enhance the new monument's meaning. This pairing shows the continued stakes of the history of exploration in the Early Modern period, as the encounters in Nigeria that made the plaque possible and placed it in the Met makes necessary the monument by the Nigerian-American artist in the former Confederate capital.